DE60009382T2 - Kationischer Azofarbstoff für Tintenstrahltinte - Google Patents

Kationischer Azofarbstoff für Tintenstrahltinte Download PDF

Info

Publication number: DE60009382T2
Authority: DE; Germany
Prior art keywords: groups; group; substituted; ink; composition according
Prior art date: 1999-04-26
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

DE60009382T

Other languages

German (de)

English (en)

Other versions

DE60009382D1 (de

Inventor

Steven Rochester Evans

Csaba A. Rochester Kovacs

Helmut Rochester Weber

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Eastman Kodak Co

Original Assignee

Eastman Kodak Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1999-04-26

Filing date

2000-04-14

Publication date

2005-03-10

2000-04-14 Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co

2004-05-06 Application granted granted Critical

2004-05-06 Publication of DE60009382D1 publication Critical patent/DE60009382D1/de

2005-03-10 Publication of DE60009382T2 publication Critical patent/DE60009382T2/de

2020-04-15 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

125000002091 cationic group Chemical group 0.000 title claims description 24
239000000987 azo dye Substances 0.000 title claims description 6
239000000975 dye Substances 0.000 claims description 51
239000000203 mixture Substances 0.000 claims description 32
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
125000004432 carbon atom Chemical group C* 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 13
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 12
125000003118 aryl group Chemical group 0.000 claims description 12
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
125000003710 aryl alkyl group Chemical group 0.000 claims description 9
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical group CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 9
239000003906 humectant Substances 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
125000003277 amino group Chemical group 0.000 claims description 4
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 4
125000002837 carbocyclic group Chemical group 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
125000004442 acylamino group Chemical group 0.000 claims description 3
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 3
125000004663 dialkyl amino group Chemical group 0.000 claims description 3
125000005117 dialkylcarbamoyl group Chemical group 0.000 claims description 3
229940028356 diethylene glycol monobutyl ether Drugs 0.000 claims description 3
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
125000001072 heteroaryl group Chemical group 0.000 claims description 3
JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 claims description 3
125000005496 phosphonium group Chemical group 0.000 claims description 3
125000001453 quaternary ammonium group Chemical group 0.000 claims description 3
125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 3
QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 claims description 2
125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 2
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
150000001450 anions Chemical class 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
125000004986 diarylamino group Chemical group 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
238000005956 quaternization reaction Methods 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims 1
239000000976 ink Substances 0.000 description 47
-1 hydroxyethyl groups Chemical group 0.000 description 25
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
238000000034 method Methods 0.000 description 8
239000003086 colorant Substances 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
230000007935 neutral effect Effects 0.000 description 6
239000007787 solid Substances 0.000 description 6
239000000126 substance Substances 0.000 description 6
238000007641 inkjet printing Methods 0.000 description 5
239000001043 yellow dye Substances 0.000 description 5
239000003139 biocide Substances 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
230000000052 comparative effect Effects 0.000 description 4
239000004310 lactic acid Substances 0.000 description 4
235000014655 lactic acid Nutrition 0.000 description 4
239000000243 solution Substances 0.000 description 4
239000000758 substrate Substances 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
0 C[C@@](C=C(N(C)*)N=Nc1c(*)[n]c2c1C=CC(C)(*)C=C2)C=[N+] Chemical compound C[C@@](C=C(N(C)*)N=Nc1c(*)[n]c2c1C=CC(C)(*)C=C2)C=[N+] 0.000 description 3
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LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
230000009102 absorption Effects 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
230000003115 biocidal effect Effects 0.000 description 3
XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
150000003839 salts Chemical group 0.000 description 3
239000002904 solvent Substances 0.000 description 3
BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical compound C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 2
SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
239000013543 active substance Substances 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 description 2
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 2
238000004040 coloring Methods 0.000 description 2
SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000001041 dye based ink Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
235000019441 ethanol Nutrition 0.000 description 2
LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
239000000835 fiber Substances 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
238000007639 printing Methods 0.000 description 2
239000000047 product Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 2
ITBWPVAUWLFXIO-UHFFFAOYSA-N (2,3-dimethyl-1-phenyl-3h-pyrazol-5-yl)-(2-methyl-1h-indol-1-ium-3-yl)diazene;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.CN1C(C)C=C(N=NC=2C3=CC=CC=C3[NH2+]C=2C)N1C1=CC=CC=C1 ITBWPVAUWLFXIO-UHFFFAOYSA-N 0.000 description 1
AWRNNIGAJXBTSG-UHFFFAOYSA-N (2-methyl-1H-indol-3-yl)-(5-methyl-2-phenylpyrazol-3-yl)diazene Chemical compound Cc1cc(N=Nc2c(C)[nH]c3ccccc23)n(n1)-c1ccccc1 AWRNNIGAJXBTSG-UHFFFAOYSA-N 0.000 description 1
CNKXSGBFDSBULR-UHFFFAOYSA-M (e)-n-[(z)-(2,4-dimethyl-1,2,4-triazol-3-ylidene)amino]-1-methyl-2-phenylindol-1-ium-3-imine;chloride Chemical compound [Cl-].CN1C=NN(C)\C1=N\N=C\1C2=CC=CC=C2[N+](C)=C/1C1=CC=CC=C1 CNKXSGBFDSBULR-UHFFFAOYSA-M 0.000 description 1
ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical group COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
QAMCXJOYXRSXDU-UHFFFAOYSA-N 2,4-dimethoxy-n-[2-(1,3,3-trimethylindol-1-ium-2-yl)ethenyl]aniline;chloride Chemical compound [Cl-].COC1=CC(OC)=CC=C1NC=CC1=[N+](C)C2=CC=CC=C2C1(C)C QAMCXJOYXRSXDU-UHFFFAOYSA-N 0.000 description 1
SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical group COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical group COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
NECRQCBKTGZNMH-UHFFFAOYSA-N 3,5-dimethylhex-1-yn-3-ol Chemical compound CC(C)CC(C)(O)C#C NECRQCBKTGZNMH-UHFFFAOYSA-N 0.000 description 1
FMKMKBLHMONXJM-UHFFFAOYSA-N 5-methyl-2-phenylpyrazol-3-amine Chemical compound N1=C(C)C=C(N)N1C1=CC=CC=C1 FMKMKBLHMONXJM-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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229920002972 Acrylic fiber Polymers 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
239000004129 EU approved improving agent Substances 0.000 description 1
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241000233866 Fungi Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
JSJWCHRYRHKBBW-UHFFFAOYSA-N N-carbamoyl-beta-alanine Chemical compound NC(=O)NCCC(O)=O JSJWCHRYRHKBBW-UHFFFAOYSA-N 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
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239000002202 Polyethylene glycol Substances 0.000 description 1
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239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
238000000862 absorption spectrum Methods 0.000 description 1
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
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150000001298 alcohols Chemical class 0.000 description 1
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125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
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229910021529 ammonia Inorganic materials 0.000 description 1
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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KSCQDDRPFHTIRL-UHFFFAOYSA-N auramine O Chemical compound [H+].[Cl-].C1=CC(N(C)C)=CC=C1C(=N)C1=CC=C(N(C)C)C=C1 KSCQDDRPFHTIRL-UHFFFAOYSA-N 0.000 description 1
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000005540 biological transmission Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 1
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150000001875 compounds Chemical class 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
229910021641 deionized water Inorganic materials 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
238000000502 dialysis Methods 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical group COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical group CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
239000000982 direct dye Substances 0.000 description 1
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238000011156 evaluation Methods 0.000 description 1
238000005189 flocculation Methods 0.000 description 1
230000016615 flocculation Effects 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
229940050410 gluconate Drugs 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
238000003384 imaging method Methods 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
238000009434 installation Methods 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
229940035429 isobutyl alcohol Drugs 0.000 description 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000002372 labelling Methods 0.000 description 1
150000003893 lactate salts Chemical class 0.000 description 1
125000006525 methoxy ethyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])OC([H])([H])[H] 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
244000005700 microbiome Species 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
239000002245 particle Substances 0.000 description 1
230000035515 penetration Effects 0.000 description 1
125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000001042 pigment based ink Substances 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920001343 polytetrafluoroethylene Polymers 0.000 description 1
239000004810 polytetrafluoroethylene Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000002243 precursor Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000000985 reactive dye Substances 0.000 description 1
230000009467 reduction Effects 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
230000007928 solubilization Effects 0.000 description 1
238000005063 solubilization Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
239000004758 synthetic textile Substances 0.000 description 1
125000005207 tetraalkylammonium group Chemical group 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
239000004753 textile Substances 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical group COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical class OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical group C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
238000000108 ultra-filtration Methods 0.000 description 1
210000002268 wool Anatomy 0.000 description 1
DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/328—Inkjet printing inks characterised by colouring agents characterised by dyes

Landscapes

Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Wood Science & Technology (AREA)
Organic Chemistry (AREA)
Inks, Pencil-Leads, Or Crayons (AREA)
Ink Jet Recording Methods And Recording Media Thereof (AREA)

DE60009382T 1999-04-26 2000-04-14 Kationischer Azofarbstoff für Tintenstrahltinte Expired - Fee Related DE60009382T2 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US09/299,412 US6136080A (en)	1999-04-26	1999-04-26	Cationic azo dye for ink jet ink
US299412		1999-04-26

Publications (2)

Publication Number	Publication Date
DE60009382D1 DE60009382D1 (de)	2004-05-06
DE60009382T2 true DE60009382T2 (de)	2005-03-10

Family

ID=23154694

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE60009382T Expired - Fee Related DE60009382T2 (de)	1999-04-26	2000-04-14	Kationischer Azofarbstoff für Tintenstrahltinte

Country Status (4)

Country	Link
US (1)	US6136080A (fr)
EP (1)	EP1052274B1 (fr)
JP (1)	JP4652521B2 (fr)
DE (1)	DE60009382T2 (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6444020B1 (en) *	1999-04-16	2002-09-03	Fuji Photo Film Co., Ltd.	Tetraalkyl-substituted nitrogen-containing hetero ring-bonded azo dye, ink-jet ink comprising said dye, ink-jet recording method using said ink, and thermal transfer recording material comprising said dye
US6174356B1 (en) *	1999-05-06	2001-01-16	Eastman Kodak Company	Dye for ink jet ink
US6468338B1 (en) *	2000-10-12	2002-10-22	Eastman Kodak Company	Dye for ink jet ink
US6464767B1 (en) *	2000-10-12	2002-10-15	Eastman Kodak Company	Ink jet printing method
US6523950B1 (en) *	2000-11-21	2003-02-25	Eastman Kodak Company	Ink jet printing method
US7160933B2 (en)	2003-03-20	2007-01-09	Eastman Kodak Company	Stable ink jet ink composition and printing method
US7033425B2 (en) *	2004-04-15	2006-04-25	Eastman Kodak Company	Ink jet ink set

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Publication number	Priority date	Publication date	Assignee	Title
US3435022A (en) *	1964-07-10	1969-03-25	Geigy Ag J R	Pyrazolone monoazo dyes containing indole or carbazole groups
US3515715A (en) *	1967-01-23	1970-06-02	Eastman Kodak Co	Quaternized pyrazolylazo dyes
US3585182A (en) *	1968-02-28	1971-06-15	Eastman Kodak Co	Quaternized triazoliumazo - 4 - phenyl-thiomorpholino-1,1-dioxide dyestuffs
DE2520816C3 (de) *	1975-05-09	1979-02-15	Bayer Ag, 5090 Leverkusen	Methinfarbstoffe
US4201707A (en) *	1975-05-09	1980-05-06	Bayer Aktiengesellschaft	Methine dyestuffs containing a phenyl azo group
FR2326453A1 (fr) *	1975-09-30	1977-04-29	Ugine Kuhlmann	Nouveaux colorants cationiques
JPS575771A (en) *	1980-06-13	1982-01-12	Fuji Photo Film Co Ltd	Formation of colored image by ink jetting method
JPS6050393B2 (ja) *	1980-06-13	1985-11-08	富士写真フイルム株式会社	水性インキ組成物
US4382801A (en) *	1980-12-24	1983-05-10	Ciba-Geigy Corporation	Process for spin dyeing polymers or copolymers of acrylonitrile with quaternized heterocyclic diazo dye and tetrafluoro-borate anion
US4929277A (en) *	1987-07-10	1990-05-29	Fuji Photo Film Co., Ltd.	Recording liquid
DE4315383A1 (de) *	1993-05-08	1994-11-10	Bayer Ag	Kationische Diazacyaninfarbstoffe
JP3451718B2 (ja) *	1993-07-08	2003-09-29	ソニー株式会社	印画紙、その製造のための染料受容層形成用組成物及びそれらを使用する画像形成方法
DE4444863A1 (de) *	1994-12-16	1996-06-20	Bayer Ag	Kationische 1,3,4-Thiadiazolfarbstoffe
GB2315493B (en) *	1996-07-24	2001-01-03	Lexmark Int Inc	Ink jet ink dyes
JPH10251577A (ja) *	1997-03-07	1998-09-22	Canon Inc	インクジェット用インク、及び該インクを用いたインクジェット記録方法

1999
- 1999-04-26 US US09/299,412 patent/US6136080A/en not_active Expired - Lifetime
2000
- 2000-04-14 DE DE60009382T patent/DE60009382T2/de not_active Expired - Fee Related
- 2000-04-14 EP EP00201351A patent/EP1052274B1/fr not_active Expired - Lifetime
- 2000-04-25 JP JP2000128964A patent/JP4652521B2/ja not_active Expired - Fee Related

Also Published As

Publication number	Publication date
US6136080A (en)	2000-10-24
EP1052274B1 (fr)	2004-03-31
JP2000319558A (ja)	2000-11-21
DE60009382D1 (de)	2004-05-06
JP4652521B2 (ja)	2011-03-16
EP1052274A3 (fr)	2002-06-12
EP1052274A2 (fr)	2000-11-15

Legal Events

Date	Code	Title	Description
2005-04-28	8364	No opposition during term of opposition
2009-02-19	8339	Ceased/non-payment of the annual fee

Publication	Publication Date	Title
DE69911894T2 (de)	2004-09-09	Metallkomplexverbindung für Tintenstrahltinte
DE60128431T2 (de)	2008-01-24	Tintenstrahl-Tintenkomposition, einen Pyrazolazoindolfarbstoff enthaltend
DE69001489T2 (de)	1993-10-21	Tinte und Aufzeichnungsverfahren unter Verwendung derselben.
DE69914296T2 (de)	2004-11-18	Tintenstrahldruck mit Metallkomplex
DE3751112T2 (de)	1995-07-13	Tinte und Tintenstrahldruckverfahren unter Verwendung derselben.
DE69801818T2 (de)	2002-04-11	Metallkomplex-Disazofarbstoffe, ihre Herstellung und Verwendung
DE60303191T2 (de)	2006-11-02	Verfahren zur herstellung von phthalocyaninverbindungen
EP0918074A1 (fr)	1999-05-26	Colorants azoiques, leur préparation et utilisation
DE69916055T2 (de)	2005-03-03	Verwendung von lithiumsalzen anionischer farbstoffe zur verbesserung ihrer lichtechtheit
EP1160291B1 (fr)	2002-02-27	Colorants azoiques, leur préparation et leur utilisation
DE60002693T2 (de)	2004-04-15	Farbstoffzusammensetzung mit hoher lichtechtheit
DE60208855T2 (de)	2006-08-31	Tintenstrahl-Tintenset und -Druckverfahren
EP2169009B1 (fr)	2011-05-25	Colorants anthrapyridones, leur préparation et leur utilisation
DE60205966T2 (de)	2006-05-18	Metallkomplexverbindung für Tintenstrahltinte
DE60022119T2 (de)	2006-06-08	Farbstoff für Tintenstrahldrucktinte
DE60209648T2 (de)	2006-10-05	Phthalocyanincyanfarbstoff mit angebrachter Chelatgruppe zur Herbeiführung von Monomerfarbstoffbildung und erhöhtem Chroma
DE60132905T2 (de)	2009-03-05	Schwarze azofarbstoffe
EP1219682B1 (fr)	2003-02-05	Colorants monoazoiques, leur préparation et leur utilisation
DE19711443A1 (de)	1998-09-24	Wasserlösliche Chinacridone
EP2468822B1 (fr)	2015-06-10	Colorants noirs triazoïques, leur préparation et leur utilisation
EP1031614B1 (fr)	2003-01-08	Colorants monoazoiques, leur préparation et leur utilisation
US6136080A (en)	2000-10-24	Cationic azo dye for ink jet ink
DE60207791T2 (de)	2006-08-31	Farbstoffmischung fur Tintenstrahltinte und Druckverfahren
DE19845640A1 (de)	2000-04-06	Azofarbstoffe
EP1048701B1 (fr)	2004-04-07	Encre pour impression par jet d'encre contenant un colorant azo cationique délocalisé